My Name is Charlene and this is a true story about my first transgender experience.
The year was 1978 and the gay and lesbian scene was really coming out into the forefront. I was very straight, at least I thought I was. I was hanging out with a crowd that was mostly actors in Chicago at the time. I was hustling a very sexy actress at the time but the group had another idea for me. They had pushed me a little to hang around the gay scene but frequently backed off if I balked at the environment.
I heard endless stories about their gay encounters, cock size, intimate details of anal sex etcetera. I was actually appalled by most of it but put up with the embarrassment, trying to get into the actresses pants. I still had no inclination toward gay lifestyle.
For weeks this went on, we met as a group, we went to dinner, we went to gay bars, the guys left copys of Blue Boy magazine out for me to read, anything to entice me into their lifestyle.
Let me describe myself. At the time I was a very butch, athletic type man with a hairy chest, wide shoulders and a slim waist.I had no idea how appealing I was to the male population. I was too obsessed with my shyness for the fairer sex. I wanted nothing more than to sleep with the actress de jour.
The whole gay/actor scene somehow escaped me, I knew many actors were gay but I assummed all actresses were straight. Hell I was 27 and in my prime and on a mission.
One night the group invited me to join them at a jazz concert of a local jazz vocalist. I was a huge jazz afficionato, so I readily agreed, being un aware that the artist drew a very gay and transgendered audience.
I was enthraled by the performance, I was sipping beers and enjoying myself emencecely, ignoring the gay jabs and inendo. After an hour or so I needed to go to the bathroom and this brought a big uproar from the gay contingint. They all teased and cojoled me into going to the girls room instead of the mens room. Thery said in a gay bar, the men go femmme and the femes go male.
All the way to the restroom I was in a quondery, do I do whats normal or appease my friends?At the last moment I decided to go into the womens room, thinking, I could beat up anyone who made advances.
Imagine my suprise as when I entered that there were nothing but women in the rest room. I headed directly for the stall, when one of the women spoke to me and said in a deep voice, "Hi handsome."
I took a quick look at the other two women and realized that they were men as well. I was totally off my game, I found myself turned on and appalled at the same time. Before me stood a very sexy man with shoulder lenth black hair and a black and white print high thigh length dress. If not for his voice I would have been fooled completely. Out of the stall came a beutifull woman in a red dress, cut to her high thighs, in a blonde wig and bright red lipstick. Despite myself I began to feel an erection.
The girls were very aware of my situation and instead of teasing me like my friends, they treated me like a human being and acted like women. We exchanged small talk while I went into a both and peed and they primped their hair.
I don't know how it happened but they invited me to another after show party. Whether they knew my situation, or they just were very warm and seasoned transexuals, I will never know but they said why don't you meet us at this address and slipped me a card with a nearby address.
I rejoined my friends and took the ribbng for going to the womens room.We sat through another set of the singers wonderfull jazz vocals. When she broke for her third set, I told everyone I had to go and they assummed I was uncomfortable with the scene and hugged me and let me go.
I went outside and asked a cab driver to take me to the address on the card. We only went about a mile before he let me out infront of a four flat brownstone near Wriggley field.
Twice I walked away before ringing the doorbell, but three times I came back, remembering the feeling in my gut when I entered the womens room. Elizibeth the one in Black and white answered the door after I finally gathered the nerve to ring the door bell. She smilled warmly and said, "we were hopping you would join us." No touching, no kissing, just a sweet smile.
Upstairs I entered to see the three same women/men I had seen in the womens room, along with a very femminane man dancing with the other two. They all smilled and kissed my cheek as I was introduced to each in turn.
Needless to say I was very uncomfortable, so Elizibeth took me to the kitchen and made me a strong bourbon and water. I took a healthy swig and tried in vain to relax.
Elizibeth took my hand and looked me in the eyes and said, "You are among friends", we will not do anything you don't want to do. We are good people!"
This made me relax somewhat but I was still on edge, my dick said let's go, but my mind said, they are men and this is wrong. I slowly exited the kitchen and found a seat near the living room. I watched the three girls dance and gyrate and grind agaist each other untill the booze took effect and I realized I was at full attention, thinking of the women as women.
The femme man, came over and introduced himself as Hermees,l and gave me a soft kiss on the cheek. With that he kissed everyone goodnight and let himself out.
I was in a sweet stooper and totally relaxed, as Elizabeth came over and said, lets go in the kitchen and do a shot!
I sat there doing shots and getting to know Elizibeth, Helga and Maria as we toasted nonsense. They grew more pretty as the shots went down and soon I found myself not even thinking of them as men but as the sweet women they were.
I found myself kissing Elizibeth in the kitchen and nearly gagged on her tongue, when I felt my pants come down and my hard dick was being suctioned y someone.
I guess I lost all moral diretion as we all tumbled into the bed and used all available sex organs to satisfy each other.
I awoke guilty and satisfied,k my onlyh thought was m"Fuck the Catholic's". This was a night no man should have missed.